I'm a member of the Forbes' tech team and a San Francisco-based reporter covering the agitators of the e-commerce world. I started at Forbes as a member of the wealth team, putting together the magazine's well-known World Billionaires and Forbes 400 lists. I've worked at a number of publications including The New York Times, Bloomberg News, The Orange County Register and the Half Moon Bay Review, though my first fix for news came as a student reporter at The Stanford Daily. My other duties here include covering the music business and continuing to assist our global wealth team. Follow me on twitter @RMac18 and feel free to send story ideas or tips to RMac[at]forbes[dot]com. PGP key: http://pgp.mit.edu:11371/pks/lookup?op=get&search=0x407F01B5399464FD

Forbes' 'Masters Of The New Universe' 14 Years Later

In July 1998, Jeff Bezos, sporting a tuft of hair, Wayfarers and a surfboard, appeared in a Forbes cover story entitled “Masters Of The New Universe.” Then worth $2 billion, the Amazon founder and 12 other Web entrepreneurs were riding an Internet wave that seemed endless.

“They didn’t wait around for the Internet to prove itself as a commercial medium before jumping in with both feet,” wrote Forbes’ Eric Nee. “Each started his own company… All of the companies are public, have solid holds on their markets and together have created $22.7 billion in new wealth.”

Fast forward 14 years and one dot-com bubble later and the Internet has changed. Bezos, now worth $18.4 billion, and some other “masters” have managed to hold on to their boards and continue to ride the wave. A few who Forbes highlighted back then lost their footing long ago and are now tumbling around in the Web whitewash. The Internet hasn’t been as kind to everyone as it has to the Amazon chief, who is back on the cover of Forbes this month (See my colleague George Anders’ story here).

So, what destined the man who perfected the online marketplace—and the others winners—for longevity in the ever-changing World Wide Web?

Perhaps it was age. Back then, Bezos was a mere 34, allowing him to learn and grow with Amazon. Now at 48, he’s in his prime and could lead the online retailing giant for another 15 years without blinking an eye.

Jerry Yang, then a smiling 29-year-old, crafted Yahoo! into an Internet brand with a current market cap of $18 billion, and made himself a billionaire. Among the most successful of the 13 people highlighted not named “Bezos,” Yang appeared on the cover of Forbes shortly after he and Yahoo! passed on an opportunity to license Sergey Brin and Larry Page’s PageRank technology. It would prove to be a costly mistake. Google’s Brin and Page each have personal fortunes that hover around Yahoo!’s market cap, while Yang was sent packing from Yahoo! in January after failing to steer the company he founded off the rocks.

Sky Dayton, who at 26 was the youngest of the Masters, was also one of the most intrepid. The leader of Earthlink—then gunning to be the second largest Internet service provider behind AOL—he left day-to-day operations at the company in 1999 and went on to launch four other companies including Helio and Business.com. His most recent venture, Boingo, a Wi-Fi hotspot provider went public last May.

“It is interesting to see how the [the Internet] has evolved,” says Dayton, who mocked the glasses and pleated pants for the 1998 cover photo. “There were people back then that still thought the Internet was kind of a fad. They said it would come and go.”

Among those under 30 at the time, Joe Firmage was the exception. The founder and CEO of USWeb, an online consulting firm valued at $800 million in 1998, he left the company in 1999 to further investigate his theory that all technology came from extraterrestrials. He has since toned down his foray into alien-awareness to start a series of web sites aimed at understanding and connecting the cosmos.

The elder statesmen of the bunch didn’t fare as well as the younger compatriots. The oldest, Larry Rosen (then 58), quickly flamed out after the article was published and sold his online record store and iTunes precursor, N2K, to CDNow Inc. in 1999. He now runs a jazz production and events company.

Michael Levy did a little better. He took his SportsLine, an early sports news and fantasy website, through the worst of times before eventually selling the sports website to Viacom in 2004 for less than 20% of what it was worth at the height of the bubble. He tried to capture the magic a second time with a similar venture, Open Sports. That folded in 2011 after three years of operation.

While youth positioned some to be more successful, some of the 13 did not discount the role of funding. Those who had built significant backing during the late 90s survived the nuclear winter that came after the bubble burst.

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